All For The Prize!
by LadyRaven-321
Summary: Alvin needs a new way to get around, and finds out that he can win a brand new scooter from entering into a contest. This would be great, but the real problem is the type of contest it is, and what he has to do for it. *REVISED AND COMPLETE once more *
1. Default Chapter

**A different story from my regular Chipmunks fanfic: *Note* The Chipmunks/Chipettes are 14 years old in this story.**

**Alvin needs a new way to get around. He finds out that he can win a brand new scooter from entering into a contest. This would be great, but the real problem is the type of contest it is, and what he has to do for it.**

**Alvin and the Chipmunks, of course, was created and produced by Ross Bagdasarian and the Bagdasarian productions. I am not doing this for profit. **

**Enjoy the story!**

"**ALL FOR THE PRIZE!"**

**Written by Raven Child.**

**Chapter 1**

Brittany Miller opens the front door and peers into her mailbox. She pulls out a handful of envelopes and flyers that was delivered by the mailman that morning. She quickly shuffles through the usual bills and a few flyers catch her attention briefly with some of the sales they are having in stores this week. As she walks in the door she realizes that she did actually get an letter with her name on it. She let out a coo with delight as she simply tossed the rest of the mail absently on a small table that the hall phone sat on and walked up to her room to read her letter.

At first she found that the letter held some interest to her, but then her excitement turned to a 'ho hum'. _'Just another beauty contest,'_ she thought to herself. With a sigh, Brittany casually placed the letter on the table by her bed. She got up, and went to the washroom to have a shower.

OoOoOoOoOoOo

"DAVE!" Alvin called out from the living room entrance.

"What is it, Alvin?" Dave answered back in an irritated voice. He made no attempt to look up away from the mountain of papers in front of him. "I'm busy."

"This is an emergency!" Alvin cried as he came into the kitchen where Dave sat trying to go through the bills. "I need a ride to the mall. They have a sale on these radical new running shoes and I *_have_* to get them."

Dave gradually turned away from the outstanding bill in his hand and just blinked at his over demanding son. "Why don't you just ride your bike to the mall?" He finally said.

"Come on, Dave…no one rides their bike to the mall anymore!" Alvin whined, rolling his eyes skyward.

"Oh, forgive me…I always thought all fourteen year olds loved to ride their bikes." Dave then tried to turn back to his paper work.

"Dave, please…just drive me to the mall." Alvin demanded.

"And I said, 'I'm busy'. Maybe tomorrow we will go to the mall."

"But by then it'll be too late. The sale is just for today."

"Then I'm sorry Alvin, but I need to get these bills paid up today, or we may not have power tomorrow." Dave stated.

"You know all of this could have been avoided if I had my license and a car by now." Alvin crossed his arms in protest.

"And you know you are not allowed either till you sixteen, Alvin."

"This sucks." Alvin spat as he finally left his dad alone.

Dave simply shook his head and went back to the bills. "Teenagers…" he groaned.


	2. Chapter 2

**Chapter 2**

Brittany had just finished blowing her hair dry with the dryer when the doorbell rings. She saunters down the stairs to see who is at the door. When she sees who it is through the side window, Brittany rolls her eyes skyward. She unlocks the door and opens it.

"What do you want, Alvin?" She groaned.

Alvin walked in, he ignored the irritable look Brittany was giving him and begins to talk about his problem.

"It's Dave, Brittany." Alvin started. "I went to him just fifteen minutes ago to ask if he'd drive me to the mall. You see there are these really awesome shoes they have on sale there and it is only on sale for today! When I asked him to give me a ride he refused."

"So, what's your point, Alvin?" Brittany huffed.

"…So, my point is, he just assumed that riding my bike would be acceptable to ride to the mall. Only geeks do that these days." He finished, waving his arms up in the air.

"I don't mean to be rude or anything, but I have my own problems, Alvin." Brittany argued. "I'm at a fashion dilemma here. My whole wardrobe needs to be updated, and I have no money to buy new clothes…I am doomed to wearing last season's style." She whined as she wonders back up the stairs and into her room.

"My heart bleeds for you, Brittany." Alvin muttered as he followed her. "But we are listening to my problems right now."

"Listen," Brittany begins as she starts to toss her old clothes out from her closet and onto her bed. "I did not invite you over, you just came. And now you expected to have me listen to you when you can see that I am in the middle of something important here?"

Alvin gave Brittany a hurt look, and somehow she felt a little sympathy for him. "Alright Alvin," Brittany sighed. "I'll listen, but you have to help me move some of these clothes to the attic, ok?"

"Fine," Alvin reluctantly agreed. He walked up to her bed and watched for a moment as Brittany threw more clothes onto the bed. Something catches his attention and that is when he noticed a letter by her bed. "What's this, Brittany?" He asked as he began to read the strange letter.

"Oh, that is from this pageant that is happening in six months. It is an invitation to participate, but I have far too much to do and the prize doesn't really interest me much."

"Whoa! First prize is Motor Scooter?" Alvin took notice right away and looked up at Brittany. "This could be the answer to all my transportation problems."

Brittany caught the 'I have a plan' look and began to back away from Alvin. "No way Alvin. I read the qualifications and what I would need to go through in that contest and I refuse to do anything that is degrading to my already beautiful self."

"Come on, Brittany…" Alvin began to plead. "We can share the prize?"

"Share? Us?" Then Brittany started to laugh out loud.

"Your enthusiasm astounds me, Brittany." Alvin growled. "Fine, if you won't help me, then I'll ask Jeanette or Eleanor to help."

"If you think that they will help you with this, Alvin, then you're dreaming." Brittany laughed again.

"Well, why don't I just ask them?" Alvin suggests as he begins to walk out the room with the letter in his hand.

"Sure; be my guest," she chuckled in amusement.

OoOoOoOoOoOo

Alvin walks down the stairs and into the kitchen. The first chipette he runs into is Eleanor. She is just pulling out freshly baked muffins out of the oven. Alvin walked in a gleam of hope in his eyes. He waves the letter in the air as he walked straight up to Eleanor.

"Say Ellie, how do you feel about entering a contest with me?" Alvin tried with a sales pitch to the youngest chipette.

The blond pigtailed chipette raised her eyebrow in suspicion to the smooth talking chipmunk. "What are you talking about Alvin?" She said in a cynicism tone in her voice.

"I'm talking about this, Eleanor. It is a chance of a lifetime experience and an opportunity to exceed in stardom." He offered her. "As me as your manager you are a sure-win in this beauty contest."

"Beauty contest?" Eleanor echoed. "Alvin, have you gone insane? I am not participating in any beauty contest."

"Come on, Ellie…" Alvin turned to begging.

"I'm sorry, Alvin. I don't have time. Between my classes and after school soccer practice there is just no room for any beauty contests." She said as she carefully takes out each freshly baked muffin out of the tray.

"But Eleanor," Alvin persisted to beg.

"Alvin, no is my final answer. Now if you don't mind I need to get the next batch of muffins in the oven. I'm taking them to my teammates tomorrow during soccer practice."

In defeat, Alvin leaves the kitchen with his head hung low.

A glimmer of hope suddenly walks by, however. Jeanette had got up from the couch in the living room to head up the stairs. Alvin stopped her at the foot of the stairs with wide grin on his face.

"Alvin, oh hi," Jeanette said with a startled look on her face. "I didn't notice you were there. Is there something I can help you with?"

"You sure can, Jeanette. You can help me win this contest." Alvin said convincingly.

"Huh? What kind of contest?" Jeanette asked, backing up away from the young chipmunk.

"A beauty contest… and as me as your manager…"

"Oh, no…" Jeanette interrupted him. "We did this before and look what happened."

"Yeah, you won, remember." He said thinking back a few years ago when they were in elementary.

"Maybe so, but the whole experience was just miserable. I told you before and I'll tell you again, I'm not the beauty type. I'm sorry, but no is my final answer." Before Alvin could talk her into it, Jeanette rushes up the stairs to hide in the spare room.

Once again, Alvin is where he started. An opportunity is sitting in his hand and yet no contended to participate in helping him win the prize of a motor scooter.

Alvin returned to Brittany's room with a frown on his face. He absently shoves the letter in his pocket as he walks back into Brittany's room. Brittany gave him a gloating look.

"Told you." She smirked. "Now that your done trying to recruit everyone in your schemes, you can focus again in helping me move some of these clothes up to the attic…here you start taking these up."

Brittany handed Alvin a large arm full of her dresses, three blond wigs, and two pairs of high heeled shoes. With a heavy sigh, he heads for the stairs that lead up to the attic he paused for a moment. If none of the Chipettes wanted to help him with this pageant, then who else would do it? He looked at the cloths in his arms and then an idea came to him. With a devilish look on his face he passed the stairs to the attic and ran down the main stairs and out the front door with the dresses still in his arms.

"Alvin?" Brittany called out when she heard the front door close. When he did not answer her she assumed that he went home to pout. She shrugged her shoulders and went back to organizing her wardrobe.


	3. Chapter 3

**Chapter 3**

When Alvin came home he quickly ran upstairs to lay all of Brittany's 'borrowed' clothes out on his bed. As he pondered over each item he held them up to have a better look over the details. He figured that he himself could fit in them easily.

To be sure this would work, Alvin quickly made sure no one would be around to walk in on him. He closes the door then ran back to his bed. He first took off his shoes and hat. After he pulls his bright red sweater with a capital "A" on the front of it over his head then he slips out of his blue jeans. He then picked up the pair of high heel shoes that Brittany threw in the pile. They were barely a perfect fit, just a little tight around the toes. Then he threw on one of the wigs she had for when Brittany wore when she acted in a play last year. Alvin even picked up one of Brittany's corsets from the pile. At first it seemed straight forward in putting on the tight undergarment, but soon he began to struggle as he attempted to buckle on each button from the bottom, up. With each different angle he squirmed, he just couldn't get it to fit right. Alvin started to sway from side to side in order to keep balance in the heels he was in.

Five minutes have passed and he was still struggling with his corset. There seemed to be no end to this discouraging piece of wardrobe. "How do women do this?" He wondered out loud.

Simon walked in and froze in his tracks. He stared shock at what his brother was doing. This isn't the first time he seen Alvin doing something this nutty before, but something about his older brother trying to put on a corset while wearing a blond wig and red high heeled shoes doesn't seem normal, even for him.

Simon wasn't sure what to do. Would he scream? Laugh? Or just turn around and walk away in disbelieve? Finally he had to say something.

"Alvin, what on earth are you doing?"

Alvin turned in utter humiliation. His face never looked so red. What could he say to his smarter brother? Then he thought up a devious plan. "Simon, I need help."

"There's an understatement." Simon muttered to himself, as he backed away knowing what would happen next. Suddenly he wished he'd just backed away when he had the chance.

"Simon, there is this contest and the first prize is a brand new motor scooter. I have to have it! It will solve my transportation problems and I won't have to bother Dave for rides all the time." He pleaded to his brother.

"And this has to do with you putting on a corset…how?" Simon moved his hand in a circle motion to indicate for Alvin to get to the point.

"That's just it…It is a contest for girls."

"Then why don't you go get Brittany, Eleanor, or Jeanette to enter for you?" Simon asked in an irritated voice.

"Because they don't want to do it…Brittany says 'it's degrading'." Alvin answered in a low tone.

"And what you are about to do, isn't?" The bespectacled chipmunk cried in shock.

"That is why you have to help me Simon. You can make sure that I can pull this off…please…teach me to be a woman?"

Simon glanced at the door in which he came in, and wished he could be at the other end right at that moment. He looks back at Alvin with annoyance written all over his face.

"Alvin, this whole thing is making me really uncomfortable. This goes beyond any of your usual hare-brained schemes."

"Simon help me, I'll do anything you want. Give you whatever you need! Just please, help me?" Alvin pleaded as he fell at his brother's feet.

Simon smiled inwardly, but kept a serious look on his face as he enjoyed seeing Alvin groveling at his feet. He then lets out a deep sigh. "If I help you, it will cost you… Greatly…"

"YES! Anything! I…" Then Alvin paused, he realized that Simon, being the smart one, could have a really 'evil' way to get back at him. "Like what?" He finished with a bit of regret in his voice.

Simon just smiled devilishly at him.

OoOoOoOoOoOo

The next day Alvin slaved away all day to complete not only his chores but Simon's chores as well. In the meantime, Simon started research online to study how to transform a man into a woman. He went on YouTube to watch how a woman looks, walks, acts, and even thinks.

"I wonder if this is what they mean by 'Getting in touch with you feminine side' " Simon thought as he clicked from web page to web page for more information.

He got down to the exact measurements of Alvin in comparison of the corset he will wear. Also he studied the science behind the makeup and the best to use for Alvin's furry face.

While he was online, Simon even studied through the rules and regulations required for this contest. As he read through some of the past events he found intriguing. Simon wrote down notes on how he can help his brother become the woman he always wanted to be.


	4. Chapter 4

**Chapter 4**

Alvin stood up from leaning over the tub for so long. It felt like he scrubbed for days but now Simon's chemical stained lab coat looked white again. He holds it up with a sense of pride. "Good as new." Alvin chimed to himself. With a smile he hung the coat up on the shower curtain railing then made his way to the other room where his brother is still doing research on the computer.

"Hey Simon, your coat is white again. I left it hanging in the bathroom." He said proudly.

Simon spun around on his swivel chair to face his brother.

"That's great, Alvin." He nodded, but then a devilish gleam was noticeable in his eye. "Did you remember to clean each of me beakers?"

Alvin growled in frustration. "Not yet," he said through clinched teeth. "I was just about to do that."

"Good, I'm almost done with my research, so when you get back up from cleaning my beakers we can get started."

"Finally," Alvin sighed with relief. He was about to turn to leave when Simon called him back.

"Oh Alvin, according to the pageant website you are to do a bit of dancing…"

"That's no biggy." Alvin shrugged.

"…With one of the Judges." Simon finished raising his eyebrow in slight amusement.

"Oh." This information did not sit well with Alvin.

Simon sighed and gave his brother a serious look. "You know, you could always back out of this ridiculous charade. It's not too late."

"No way," Alvin snapped quickly. "I will enter this contest, and I will win. Your job is to make sure I look great, got it?"

"If you say so," Simon said, rolling his eyes skyward. "Just make sure you do an excellent job on my beakers. I want them looking like they did when I first got them."

Again Alvin growled under his breath. It made him hot under the collar to see his brother enjoying the fact he can take him for granted. "As you wish…" he said forcefully through his clinched teeth.

"I'm sorry, what was that?" Simon taunted.

Alvin flinched before sighing heavily. "As you wish… Master…"

"Much better," Simon nodded approvingly. "You may go now."

Alvin spun on his heel and stomped his feet as he walked out of the room.

OoOoOoOoOoOo

An hour later Alvin returned after cleaning every beaker is Simon's laboratory. He froze the instant he walked back into the room. Simon was standing by his bed – holding one of Brittany's 'borrowed' pink dresses. It had a lacy collar and long sleeves. The dress itself looked to reach just above the knees.

"Are you ready?" The intelligent chipmunk asked his older brother.

"Ready for what?" Alvin asked with a suspicious glance.

"Well, we must make sure we can actually get you to fit in these dresses, don't we?"

"I suppose… Alright, give it here and I'll put it on." Alvin said, holding out his hand to take the dress from Simon.

"Ah, it won't be that easy, Alvin." Simon shook his head. He reached down on the bed and pulled up a pair of panty hose with padding on it. "I jerry-rigged these panty hose so when you put it on it will appear you have hips like a woman."

"You've got to be kidding." Alvin was in disbelief with the appearance of these strange looking panty hose.

"Does it look like I'm kidding?" Simon asked in a serious tone. "Now strip and put these on."

With a regrettable sigh, Alvin did as he was told. As he took off his shoes, socks, and jeans Simon prepared for the next step in turning Alvin into a woman.

Alvin slipped into the panty hose a foot at a time. Once he had them on he glanced over at the standing mirror. He had to admit that the padding made his narrow his appear wider – more feminine.

"Ok Alvin, turn around." Simon ordered. "I need to put this corset on you."

"Aren't these panty hose enough to give me a feminine figure?" Alvin inquired.

"Alvin please, I didn't spend all afternoon researching these pageants and the female figure for nothing you know. Now turn around!" Simon snapped.

"Fine," Alvin sighed. "Seriously, I think you are enjoying this a little too much."

"I wouldn't be doing this at all if you hadn't gotten me involved in your scheme."

"Details, details…" Alvin groaned. "Hey, not so tight!" He gasped with the sudden pressure against his ribcage.

"Relax Alvin; it's supposed to be this tight."

Simon spun Alvin around so he could get an idea how the corset looks before he helps his brother with the dress.

"Hm, the bra doesn't seem to fill out the way they are supposed to. I'll have to fix that up later." He pondered mostly to himself. "Ok, let's put the dress on." Simon said more clearly, reaching for the dress."

"Does it have to be the pink one? Why can't I try on the red dress?" Alvin whined.

"Alvin," Simon replied with an exasperated sigh.

Not about to argue, Simon went ahead and threw the dress over Alvin's head. He slipped it down his brother's body and adjusted it to fit around the corset. Simon shook his head. He is not satisfied with how the dress looked, but at least his physique looks female. Lastly, Simon reached for one of the blond wigs. He stuck it on Alvin's head.

"Ok that should do it." Simon chimed.

Alvin looked at himself in the mirror and saw his face on a female shape body. He glanced up at his younger brother with a raised eyebrow. "Aren't you forgetting something, Simon?"

"Like what, Alvin?" Simon asked.

"Like make up." The athletic chipmunk pointed out.

"One thing at a time, Alvin; I need to get an idea of what I'm working with before we need to continue with this. Besides you don't need make up to practice wearing these high heeled shoes." Simon said with a smirk as he lifted up a pair of pink high heels.

Alvin slipped them on then proceeded to pace the room a bit as he got used to the idea of wearing such awkward shoes. He stopped as soon as he heard music. Alvin turned around to see that Simon had put on a cd with classical music.

"Ah, what are you doing, Simon?" He asked suspiciously.

"Well, I thought you could practice some of the dancing required in this competition." Simon grinned. "Now, just remember I lead," he reminded him.

"Yes, I know that. It's not like I haven't acted as a woman before." Alvin groaned, rolling his eyes skyward.

"Now I'm assuming this is the kind of dancing they are going to do." The intelligent chipmunk declared.

"If you say so," Alvin once again sighed. He just didn't feel comfortable with the idea dancing with another man, little alone his brother at this moment.

Simon but his arm around his brother and the two of them danced like a couple on a date. They didn't say too much other than some suggestive advice on posture from Simon.

A few minutes passed before Alvin finally said something back to his brother. "Why Simon, I never noticed this about you before, but you have such soft hands." He commented in a teasingly manner.

"Shut up, Alvin." Simon spat back.

As the two brothers continued to dance, Theodore had just come home and was leaving the kitchen after getting a snack. Theodore took a bite from his apple when he heard music coming from the bedroom upstairs. Wondering on which of his brothers is in the room and what he is doing, Theodore makes his way up to the second level of the house.

The bedroom door was left open slightly, so Theodore peeked in slightly before wanting to push the door open all the way. The first thing he saw was Simon dancing with someone in a pink dress. At first he thought it may have been Jeanette, but she had blond hair. The angle of which he sees this strange chipette made him wonder who she is, where she came from, and why she is dancing with his brother.

It wasn't till Simon turned her around that Theodore got a better look at the face of this new chipette. He realized that she wasn't a girl after all, but his brother Alvin. He was so shocked that he nearly dropped his half eaten apple from his hand.

'What is Alvin doing in a dress…better yet, why is he dancing with Simon?' Theodore thought.

Suddenly Theodore found this scene to be hilarious and could not contain his laughter. He ended up in a round little ball, and rolled on the floor in a fit of laughter. The music apparently was too loud for any of his brothers to know that he was there.

OoOoOoOoOoOo

A half-hour later, Theodore figured it might be safe to go and see what his brothers were doing. He opened the door and to his relief, Alvin had taken off the dress and looked like his normal self with red cap and sweater with a big yellow 'A' on it.

Theodore attempted to keep a straight face as he began to eat another apple he snatched from the kitchen. Carefully Alvin and Simon eyed their younger brother with suspicion. For some reason they guessed that he knew something due to the fact that he was enjoying that apple a little too much.

"Ah, Theodore…you weren't up here earlier by any chance were you?" Alvin asked suspiciously.

"Uh, no Alvin…and I didn't see you in a dress either." Theodore said as innocently as he could, but realized too late that he said too much.

That confirmed it. Alvin and Simon knew the gig was up. Now that Theodore knew they need to find away to keep his mouth shut about it to Dave till this is all over. Simon and Alvin casually made their way towards Theodore and cornered him against a wall. Theodore hated it whenever they did this. It usually meant that they were about to get him involved with something that could involve something scary.

Alvin and Simon stood over their little brother with mischievous grins on their faces. Theodore simply struggled in swallowing the piece of apple in his mouth.


	5. Chapter 5

**Chapter 5**

Three weeks passed and now that Alvin and Simon have Theodore helping out they now have someone to help redesign the dresses. While Theodore worked on the dresses, Simon instructed Alvin on the rules and regulations of the pageant.

Dave naturally would wonder what the boys were up to and they explained to him that it was for a school play. One Saturday, Dave had to do some work at the studio. This gave the boys an opportunity to try out the full change on Alvin.

Theodore had designed a gorgeous strapless red gown that reached to Alvin's ankles. They even splurged and bought new shoes to go with the dress. The wig was pinned up with little flowers braided into it. Simon fixed the corset so the chest appeared like a woman's. The one trick used was soft balls. To get it working with the strapless dress was another challenge, but Simon got it to look very natural. It took almost two hours before the makeover had been completed.

For the next thirty minutes Alvin wondered the around the house as well as going up and down the stairs in the high heels. Every single moment, Alvin kept in character of being a female chipmunk.

"Alright Alvin, let's hear you speak." Simon requested.

"You come this way often, big boy?" Alvin cooed in a flirtatious manner to his intelligent younger brother – rolling his finger along the side of Simon's cheek and down his chin.

"Not bad. The accent could use a little work though." Simon estimated.

"How about a little _Hispania_ or _Greek_?" Alvin rhetorically asked.

"Try something a little simpler like British." Simon offered.

"Alright, _love_…better?"

"Yes."

As Simon and Theodore watched Alvin practice his sexy feminine walk, and speaking in a classy British accent, Simon pondered for a moment.

"You know Theodore, call me crazy, but I think Alvin actually has a shot at winning this pageant."

"If you say so, Simon." Theodore answered with a chuckle. To him he thought it was still too funny seeing his brother in a dress.

OoOoOoOoOoOo

Now that he is pretty much ready it was time to get him signed in the pageant. Simon thought it would be best if Alvin got dressed up to practice being a 'woman' in public. They got another blond wig so Alvin can look nice with 'her' hair down. Theodore whipped up another dress by combining a yellow dress with a red one. The combination worked beautifully.

Alvin and Simon felt it would be safer to leave Theodore at home. Knowing their little brother he might accidentally uncover Alvin's scam before he could get in the pageant. The line up seemed longer than expected; Simon and Alvin started to wonder if this would be worth it. Moments later, as they stood impatiently in the line a familiar voice called out Simon's name.

"Simon? What are you doing here?"

The two boys turned and saw the Chipettes coming their way.

"Ah…well, um…" Simon stumbled nervously. He looked over to Alvin whom just gave a shrug. He scowled at him as if to say, _'thanks for your help'_. His brain quickly came up with the perfect solution in explaining this situation. He turned back to the Chipettes with a nervous grin. "Oh, I'm here to sponsor Al-ah…Alicia here." Simon quickly thought up. "She asked me two months ago if I would help, and I thought it might be interesting, so I accepted."

"I see." Jeanette said with a bit of a jealousy tone in her voice. She eyed 'Alicia' up and down and noticed that she is quite attractive.

"No…Jeanette. It's not what you think." Simon began to wave off his girlfriend's suspicious thinking.

"Harrumph!" Jeanette scoffed and she turned away in shear embarrassment and anger. "Is *_she_* the reason why you have not returned any of my calls recently?"

"Who…Alicia?" Simon asked innocently.

"Yes, Alicia!" Jeanette snapped. "Is she your girlfriend?"

"What? No, no, is…um… My cousin…from, uh…England." Simon again thought up quickly.

"I didn't know you had a cousin from England." Eleanor inquired suspiciously.

"Actually neither did I," Alvin muttered between his teeth. He nervously smiled at the Chipettes, whom were all giving him a hard stare to see if she were really related to Simon. "It's amazing how one can find other living relatives over the Internet these days." Alvin quickly said with a feminine British accent.

"Er, right." Simon adds raising his eyebrow at his brother in drag. "Jeanette," he then draws his attention back to his girlfriend. Quickly he drags her to one side, so that they are out of earshot from everyone else. "I'll make this up to you. I promise."

"Really?" Jeanette then replied with a bright smile of hope.

Simon simply nodded; he felt pride that he could make her feel better about this weird situation.

"When this is all over I promise we that we will go for a dinner and movie, ok?" He then suggested.

"Ok." She agreed.

While Simon talked to Jeanette, Brittany took it upon herself to interrogate 'Alicia'.

"So, ah, Alicia is it?"

Alvin nodded and wondered where Brittany was headed with her interest in the character he's playing.

"Where is Alvin? I would think he'd be the one to sponsor you in this pageant rather than Simon."

"Alvin? Oh, he had something important to do. That handsome cousin of mine is so busy, but not to worry he is using his cleaver wit to ensure I am a success in this pageant." Alvin explained in character.

"I see," Brittany raised her eyebrow. Something about this chipette does seem familiar but she can't seem to put her finger on it.

"So, uh… What brings you here?" 'Alicia' asked Brittany.

"I decided after all to join the pageant." Brittany said as she stood in a 'valley girl' pose and checked her nails. "I didn't realize it before, but I found out that first prize also includes $5000 shopping spree at Beverly Hills mall. In that respect, how could I pass up that opportunity? I could defiantly update my entire wardrobe with that." She finished with a bright smile. Finally her fashion problem would be solved.

"WHAT?" 'Alicia' screeched, almost sounding completely male. "I thought you sa…"

Alvin was cut off before he could finish as Simon suddenly covered his mouth before his cover would be blown.

"Alicia…? A little competition never hurt anyone." Simon said sternly.

Alvin simply glared at his brother and growled at him.

"Wait a sec…you remind me of someone…are you sure we haven't met?" Brittany asked in a suspicious manner.

Both Alvin and Simon looked like two deer's caught in headlights. They didn't know what to say at first. "Uh, well…it is possible we might have met, ah…briefly once." Alvin added quickly.

"I don't know," Brittany shook her head. "I don't usually forget a face." She glanced down at Alicia's dress and frowned. "But dresses are another manner. Where did you get yours?"

"It was, ah, specially made for me. I have a personal clothing designer." Alicia bragged.

"Funny, it kind of looked like a combination of two dresses I used to own." Brittany scowled.

"Well, isn't that something…" Alicia said – tugging at her neck collar as it feels that the dress is starting to chock her. "Call it a coincidence?" 'She' shrugged.

The Chipettes all looked at each other then they shrugged their shoulders. "Alright then, we will see you in the pageant then." Brittany finally said in a 'snooty' tone.

"Well, Brittany…we wish you the best of luck…Come on…*_Alicia_* let's go get you signed in!" Simon said as he tugged his brother in drag to the sign-in gate.


	6. Chapter 6

**Chapter 6**

The first day of the pageant finally arrived. All the contestants parade along the catwalk in front of the judges. Alvin was a little nervous and almost tripped on his heels before ever going on stage. He wore a pink dress with white ruffles on the sleeves. Another blond wig stylishly hung over his exposed shoulders.

During the first stages of the competition Simon waited back stage nervously with Theodore. It wasn't the fact that they weren't sure if Alvin would pull this off or not, it was more that the dress they had helped Alvin into. Some parts of the dress were beginning to show signs of stress and they were worried if it might rip in front of the audience.

Theodore did his very best with what he had to work with in regards to each of the dresses, while Simon briefed Alvin on what he had to do for each challenge. The next competition was one of his specialties and looked forward to it. Alvin performed the greatest he could…as a woman. He practiced for many hours in disguising his singing voice; just so certain people he is competing against, and even fans in the audience, wouldn't recognize him. Apparently it worked and it wowed the crowd, as usual.

Meanwhile, back stage Brittany and her sisters eyed 'Alicia', whom was singing her heart out on stage. Both Jeanette and Eleanor smiled at the efforts that Alicia gave in her performance. But Brittany, on the other hand, was still having her suspicions with this mysterious chipette. It concerned her that six months ago Alvin seemed almost desperate to have either her or her sisters join this pageant. Suddenly his 'cousin' comes for a visit and she is now here in the pageant, as well as Simon and Theodore, but Alvin is nowhere to be seen.

This made her wonder…

"Wow, that Alicia is quite good." Eleanor said.

"There is just something that I don't like about her." Brittany frowned.

"Oh, Brittany, don't be jealous." Jeanette accused.

"Jealous? Me? That's absurd." Brittany blurted.

Jeanette and Eleanor both crossed their arms and stared down at their over dramatic sister.

"Ok, so maybe I'm a bit jealous." Brittany finally admitted. "But come on. Don't tell me you're just the slightly suspicious over all of this 'Alicia' business? If this is the boys' cousin, then where is Alvin? Don't you think he should be here as well, to make sure that she wins? You know that he has his eye on the scooter ever since he saw the pamphlet for this pageant."

"Well…" Jeanette and Eleanor hummed for an excuse, but they couldn't come up with an argument to their sister's statement.

"We should defiantly keep an eye on them." Brittany then looked to her younger blond sister. "Do me a favor, Ellie? See if you can find something on them in their dressing room?"

"You want me to spy? Are you nuts?"

"Come on, Ellie…for me?" Brittany pleaded – batting her eyes in an innocent fashion.

"Oh, alright." Eleanor said in a sigh.

As Eleanor left to go look in the dressing room Brittany watched intensely as 'Alicia' finished her song and listened as the audience cheered.

"One way or the other you are going down, _Alicia_." Brittany growled under her breath.


	7. Chapter 7

**Chapter 7**

Near the end of the dance routine, Alvin started having serious problems with his corset. It started becoming loose around the front. This nearly caused him to break out of character on stage. As soon as he got the chance, Alvin immediately ran off stage and grabbed his brothers and went straight for their changing room.

"What's the matter Alvin?" Theodore asked.

"What's wrong?" Alvin screeched in a panic as he struggled to keep his dress from slipping off. "I'm falling apart here!"

"Well that's an ironic twist." Simon smirked.

"Very funny, Simon." Alvin growled. He took off his wig so his head could breathe for a bit. "Will you two just help me fix this dress?"

Simon and Theodore helped their brother out of the tight dress and Theodore attempted to fix the tear that started the problem during Alvin's dancing. In the meantime Simon was fixing and adjusting Alvin's corset. First Simon had loosened it and as he did Alvin let out a deep breath as he once again felt air in his lungs.

"Aahhh, oxygen is good." Alvin sighed as he allowed his body to slump forward in relief.

"Alright, the dress is fixed." Theodore announced as he held up the sparkling red gown.

Simon was able to realigned the corset straighten out the chest. He began to re-tighten the corset. Alvin began to dread having to go through this. But he thought about the scooter that he *_will_* win after when this is all over. It was that thought in mind that made this experience seem not so bad.

"Hurry Simon, the next part of the competition is starting soon!" Alvin shouted.

"Sorry Alvin."

Just as Simon yanked at the corset's laces one last time one of the soft ball padding's popped out from a breast cup. It flew up past Alvin's head and landed by Theodore's foot. Alvin and Simon let out a gasp of surprise. Theodore, finding this incredibly amusing, started to laugh out loud in his chair.

"Simon, You can fix this, can't you?" Alvin asked in a panicky tone.

"Alvin I would have this all done sooner if you'd stop squirming so much!" Simon snapped back.

"I wouldn't squirm so much if you are not rough with putting it on so tight!" Alvin argued.

"If you don't like it, Alvin then why don't you drop out of this ridiculous charade!"

"Are you nuts? I am not going to give up the chance to win that scooter!"

As Simon and Alvin continued to argue, Theodore still laughed over the silly soft ball breast.

"Theodore…Knock it off!!" Both Simon and Alvin bellowed at once. The youngest chipmunk finally stopped laughing, but still struggled to contain a little snicker.

"It will just take a moment, Alvin, and I'll have you looking 'whole' again." Simon said as he picked up the padding and re-stuffing them back in the corset cup holders.

"Wow, they look great, Simon." Alvin chimes as he admires them in the mirror.

As soon as the fake breasts were back in place, Simon helped Alvin to get back into his dress. Just then there was a knock on their door. In hast Simon threw Alvin's wig back on his head before the door opened. Eleanor walked in with a puzzled look on her face.

"Is everything alright in here?" She looked around the room a few times before continuing. "I thought I heard Alvin in here? Where is he?"

All three boys had become suddenly silent for they had no idea how to respond to this question.

"Aaaah…" Simon and Alvin both stalled in their own thoughts and looked at each other for 'what to say'.

"Are you sure it was Alvin you heard?" Theodore asked. The question both surprised and impressed his brothers.

"Yeah, it might have been Simon here that you heard…sometimes he makes a great impression of Alvin?" 'Alicia' grinned in nervousness.

Simon just stood there and nodded in agreement with a big silly grin.

Hmm? Perhaps?" Eleanor said, not fully believing them. She began to understand Brittany's suspicions.

"Well, they are getting ready for the next competition; you better get out there Alicia." She finally said before leaving.

All three boys let out a sigh of relief after she left and continued to prepare Alvin for the next section of the pageant.


	8. Chapter 8

**Chapter 8**

The pageant was coming to a close now and so far Alvin scam had fooled everyone. While Simon was back stage and watched closely as Alvin was on stage doing his next act in front of the audience. They were nervous about going through the swimsuit competition, but with Simon's smarts they managed to pull it off without any major dramas or complications.

The three boys are now relieved that the pageant was almost over, just 20 more minutes then they will announce the winner and the whole ordeal will be over.

Meanwhile, in the dressing room, Theodore was fixing up Alvin's dress that he will wear for the announcement of the winner's speech. Without warning, Eleanor, whom has been trying all afternoon to get a chance to talk to Theodore *_alone_* without much success, knocked on the door.

Theodore squealed and dropped his needle. He wasn't expecting anyone to be coming to the dressing room for at least fifteen minutes till the next challenge was over. Being the polite chipmunk that he is he called out, "wh-who is it?"

"It's me, Eleanor." A soft voice called back from the other side of the door.

Without thinking Theodore called out again, "come in," before picking up his needle from the floor.

"Hi Theodore." Ellie chimed. "Am I interrupting something?"

"Not really, Eleanor." Theodore politely answered. "I'm just fixing my br-ah…I mean, my cousin's dress for the coronation tonight."

"Really, I must say you are doing a wonderful job, Theodore. The dress looks gorgeous." She praised him. "Speaking of which, I was wondering if you will tell me a bit more about your 'cousin'? What is she like? What part of England is she from…?" Eleanor hinted off.

"You mean Alicia?" Theodore looked up at his girlfriend innocently.

"Who else do you think I mean?" Eleanor said as she raised an eyebrow at him.

"Oh, well…Alicia is, uh, from England I believe?" Theodore stumbled as he tried to remember what his brothers told him to say. "And well…she is visiting for a bit."

"Yes, I got that…what else can you tell me about her?" Eleanor started to put the pressure on Theodore to explain the story behind his 'cousin'. The answers he was giving her made her suspicious even more and she wanted the truth…_now_.

"Aahhh, she likes fashion, and singing, and dancing." Theodore listed to her.

"Theodore isn't there anything else you know about your cousin?" Eleanor let out an exasperating sigh. She glanced over and something caught her attention. One of the dresses seemed to stick out in plain sight. Eleanor leaned over to get a closer look and instantly recognized it. "Where did you get this dress?" She cried, grabbing hold of a mauve and pink dress.

"I'm not sure, Alvin got them…I just helped fixed them up." Theodore slipped.

"Theodore, these were Brittany's dresses!" Eleanor snapped. She reached over and grabbed what was left of a black dress. "This one use to be her evening gown…only now it's all shredded up."

"Oops." Theodore was speechless. He wasn't told that they were Brittany's dresses. Now he felt so guilty.

"And another thing…where *_is_* Alvin? I haven't seen him once during this whole contest?"

"Alvin?" Theodore said as innocently as he could.

"Yeah, Alvin…_your brother_?" Ellie leaned in, giving him a querulent glare.

"He's…ah…sick?" Theo lied.

"Oh?" Eleanor was not sure if Theodore was telling the truth or not, she knew he was a terrible liar and it was just strange on how he was not giving her a solid answer.

"Uh huh, he's been in bed the whole week with, ah…the flu." Theodore tired to explain.

"I see…" At a loss for words, Eleanor thought of nothing else to say to Theodore. She looked down again at the shredded dress and a thought cross her mind. "So why did you have to ruin my sister's dresses?"

"Because Alvin needed a new dress to wear for the pageant." Theodore absently answered.

"Alvin??" That completely took Eleanor by surprise and needed to confirm that he said the sentence right. "Don't you mean, Alicia?" She corrected him with a raised eyebrow.

"Oh right!" Theodore began to sweat. "That's what I mean. Alvin couldn't be Alicia. Th-th-that would be impossible. I mean he would have to have a huge make-over to pull that off. An-and Simon would have to help him too."

"Wait, are you saying that Alicia is a *ALVIN*?"

"Heh, heh, heh, um?"

"Theodore, tell me the truth! What are you boys up too?"

"Hey, I'm just the here to fix the dresses…I don't know the actual plan, my brothers wouldn't tell me anything." Theodore cried. "You'd have to ask Simon about it." He'd thought that would be a perfect way to 'get back' at them for blackmailing him into this stunt.

Eleanor glanced down at Theodore then decided that it would be pointless in drilling him any further. The guilty look on his pudgy face told her he was suffering enough.

"Alright Theodore." She said. Eleanor then turned and left the room.

OoOoOoOoOoOo

Eleanor ran to the back stage, but couldn't find her sisters anywhere. She ran to their dressing room. It was crowded with other contestants. How the Chipmunks got their own room is mind boggling. Alvin must have bribed someone in order to get his own room.

Finally she spotted her sisters at the end of the room, but before she could get Brittany's attention one of the back stage hands came in.

"Alright, ladies! Everyone head back out on the stage. It's time for the judges to present the winner of their choice!"

All the girls headed for the stage immediately with anticipation that they would win and leave here with a brand new scooter and a $5000 gift certificate at the Beverly Hills Mall.

"Brittany, wait…!" Ellie called out.

"Not now, Ellie! I'm about to be the winner of this pageant!" Brittany waved back before blending in with the other girls in pretty dresses.

"Oh no, too late." She blurted.

"Too late for what?" Jeanette innocently asked.

"Come on, Jeanette we need to find Simon. He has some explaining to do!" Eleanor growled, grabbing her sister's hand as she follows the girls towards the stage.

As the contestants paraded one last time on stage, Eleanor and Jeanette caught up with Simon and Theodore. They were both watching their brother on stage with the other girls.

Theodore turned and noticed the chipettes walking up to them.

"Hi Eleanor, hi Jeanette." Theodore chirped.

Simon turned and smiled at them. "Come to watch and see who the winner will be?" He asked.

Eleanor turned and glared up at the intelligent chipmunk. 'How could someone that smart be so naive?' The look he was getting made Simon rather nervous and giving him the impression that she knew something.

"I just found out that 'Alicia' is *_not_* your cousin." Eleanor spat.

"Heh, heh… Ah, why would you say that?" Simon said as he tugged at his blue turtleneck for it suddenly seemed far too tight around his neck.

"Oh, a little song bird told me." She added with her hands on her hips and her foot tapping on the floor.

"So if Alicia isn't Simon's cousin then who is she?" Jeanette said in a jealous tone. This made Simon feel as if he were being cornered. Theodore simply hid himself behind Simon, he became suddenly frightened of the chipettes.

"She…ah…is…um?" Simon stumbled.

"'She' just happens to be a 'he', Jeanette." Eleanor cut in.

"WHAT?" Jeanette now was really confused with all of this. She then looked at Simon with fury written on her face.

"I-I-Its not what you think, Jeanette." Simon tried to explain.

Inch by inch the two girls walked Simon and Theodore up against the wall. "Come clean, Simon! What is going on?" Eleanor barked. "Either you tell her, or I will."

"Ah, well…" Simon dawdled to complete his sentence, for the first time he was a loss for words.

"I'm almost afraid to ask what you are doing with 'Alicia'?" Jeanette spat.

Simon then let out a deep sigh. He knew that the jig was up with these two and it would be safer to tell the truth instead of lying more…besides the fact that the contest would soon be over and they are about to announce the winner.

"Alicia is actually Alvin in drag." Simon finally said in a low tone.

"WHAT?" Jeanette was completely shocked again at what she just heard.

"Why would he want to do this, Simon?" Eleanor cried.

Simon shook his head as he explained. The more he thought about this the more he became embarrassed in being a part of this stunt. "He-he wants to win that brand new scooter. That way he can have something to ride around in and he wouldn't have to ask Dave to drive him everywhere." He sighed.

"Theodore was right, Alvin is *_sick_*…in the head." Eleanor huffed.

"AND THE WINNERS ARE…" called out the host on stage.

At that moment Jeanette and Eleanor diverted their attention from Simon to what the announcer had to say.

"THIRD PLACE GOES TOO…JILL HAMLTON!"

The audience cheered as the girl got a third place prize. She waved to the crowd, pleased that she got this far in the program.

"SECOND PLACE GOES TOO…BRITTANY MILLER!"

Brittany tried not to look disappointed as she received her second place prize. She smiled and waved to the crowd, being as 'professional' as possible.

"AND OUR WINNER OF FIRST PLACE GOES TOO…ALICIA STINFIELD!"

The crowd cheered as 'Alicia' is being crowned and given a bouquet of flowers.

"I won?" Alvin responded with tears of joy.

"Heh, heh, heh. Well, what do you know?" Simon shrugged. "He won," he added looking at Theodore in disbelief.

"Brittany is not going to like this when she finds out the truth." Eleanor points out.

Simon took on this opportunity to sneak away as the two girls were not looking. He grabbed Theodore's arm and headed straight for the back door.

"What about, Alvin?" Theodore asked when they got outside.

"Awe, Alvin's a big 'girl'… He can take care of himself." Simon smirked.

OoOoOoOoOoOo

"…And I just want to thank you for your support and appreciation you have given me! This really means a lot! Have a great evening, Goodnight everyone!" Alvin said to the audience.

One of the judges gave him the key to the brand new scooter. Alvin grins devilishly at it in his hot little hand. The judge also gives him a certificate for $5000 shopping spree. Dollar signs flashed in Alvin's eyes as his smile widened. He even receives a bouquet of flowers in the other hand.

"Why, thank you." Alvin smiles up at the judge before making his hasty retreat on the scooter and drove it off the stage. The audience kept cheering.

Alvin made it outside and stopped to see if his brothers were waiting for him so he can gloat. When he noticed that they weren't anywhere to be seen, he figured that they went to clean out the dressing room.

He started up to the new scooter and tossed the flowers in a nearby trash can. Before Alvin managed to drive away the Chipettes stood in front of him.

"Congratulations on winning this prize." Brittany scowled.

"Oh, well thanks." Alvin blushed as he beamed with so much pride he failed to notice all three girls was glaring at him. "Say, you three haven't seen my, uh, cousin's…Simon and Theodore…have you?"

"Actually they left." Jeanette stated.

"Well, that's gratitude for you." Alvin growled irritably.

"Oh, I wouldn't be too concerned with them…we know your little secret." Eleanor growled.

"R-r-r-really? And what secret is that?" At this point Alvin began to take notice on the expression on the girl's faces. This made him very nervous.

"My sisters just told me you're not a girl after all, are you… Alvin!" Brittany spoke angrily.

"Oops, gotta go." Alvin accelerated and swerved so fast that his wig flew off his head.

As Alvin sped away on his prize he heard Brittany screaming at the top of her lungs while she ran after him.

"**AAAALLLLL-VVVIIIIIIIIINNN!!!!!!"**

The End! :-P


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